


8 out of 9 Times

by Caketastrophe_cosplay



Category: Critical Role (Web Series)
Genre: Angst, Backstory, Bad Dreams, M/M, Masturbation, Multi, Mutual Pining, Nightmares, Pining, Romance, Sad Backstory, Sex, Smut, Spoilers, Yasha is a good friend, bad choices, dirty wizard boy is shy, emptyiness, lots of fluff, mollymauk is shameless, mollymauk is stupid but for entertaining reasons, nipple rings, piercings galore
Language: English
Status: In-Progress
Published: 2018-04-29
Updated: 2018-05-30
Packaged: 2019-04-29 12:31:54
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,543
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14472822
Author URL: https://archiveofourown.org/users/Caketastrophe_cosplay/pseuds/Caketastrophe_cosplay
Summary: The eight times Molly got his nipple rings caught on something and the one time he didn't.Posted in sets of two little stories at a time and moving chronologically through the adventure.





	1. The First Two

**Author's Note:**

> Truthfully this was inspired by Liam asking deliberately in episode 16 if Mollymauk had nipple rings in and Taliesin replied that "No those get caught on things. they're dangerous!" Which of course led me to think that molly definitely had them at one point until they became too annoying as an adventurer and he took them out. 
> 
> So here are the eight times Mollymauk Tealeaf got his nipple rings stuck on random objects and the one time he finally didn't. Enjoy.

Mollymauk Tealeaf went through many appearance changes in the first year of his new life. It had taken many trial and errors to figure out what kind of person he was to even begin with and what kind of person he wanted to be on the outside to reflect his new found identity. It became very clear to him very quickly that he enjoyed fucking with people for the pure joy of watching them react and to create interesting situations. Call it childish, whatever, he was technically two years old anyway, but it gave him joy and happiness and he would take anything that could replace the horrible feeling of empty he'd had for the first month of his new life. 

The circus was his inspiration for a lot of his fashion choices but his body modifications came from a desire to shock anyone that saw him. He was already a flamboyant purple tiefling and he enjoyed standing out so why not make it even better than before. He wanted to be shiny too.

It started simply with his ears getting pierced. That was quickly followed by the tattoos, anything to cover up the god awful red eyes that littered his right arm and neck. He didn't want to see anything from the asshole that got himself dumped in the dirt. However the tattoos and ear piercings only did so much, so the horns were pierced shortly after, he rocked a lip ring for awhile and then found his fangs kept clipping it so he ditched that one. Then he wanted more ear piercings so he just kept going up the sides.

Eventually he went as far as getting his nipples pierced because he knew he was pretty and he knew his nipples were pretty and what better way to show off then have the rings show just slightly through his undershirt because the material was certainly thin enough for that. 

At first they were worth it and then very quickly into the two years he had them they became a problem. A big problem. 

________________________________________________________________

1\. Yasha's Hair

 

It had been a rough day for all of them, a full three days of continuous travel between the two towns that they were trying to make haste in-between. The previous town had enjoyed their presence but the crowns guard had made it clear that on their last night of their show they better be out of there by the morning. It was nothing they weren't used to because hey, they were carnival people and as Molly liked to think, they were weird. 

He was still walking a fine line between re-learning how to read and write with Yashas help, and building up stories about his childhood that were believable and concrete. He needed to have a list of many to help in any situation he might find himself in, even with his carnival family. Only Yasha and Gustav had any idea that he was a walking void with nothing to fill his head. 

The silence was the worst, which is why he had taken to making up fantastical stories about himself and what he had done. As they walked along the road, the next town in sight on the horizon, he was jostled from his thoughts by the strong and silent woman who approached his side. 

"How are you doing Molly?" He grinned as wide as was possible up at her, continuing to shuffle the cards in his hands as he walked. The cards had become fundamental to him in guiding him towards something he could be. They had given him something that was his own, a hobby, a story and the power to tell others stories to them. Most people were self centered enough to want to know about themselves more than him and he could live just fine with that.

"Oh absolutely wonderful. Ready to set up in the next town, it will certainly be exciting." Yasha nodded silently to that but she did reach up and place a hand on his head and rustled his steadily growing hair. It was just to his ears now and he was determined to keep growing it. He could not fathom why someone would shave off such beautiful plum colored curly hair. It was growing in beautiful waves with little curled ends now that it was getting longer but oh man it had been absolute hell when it had only been about an inch long. He had almost shaved it off again but Yasha had reminded him about how much he had hated it like that. 

"Good. We should be able to set up soon."She was staring at the horizon as he replied. He nodded at that and remembered his gift he had acquired for her earlier.

"Ah I almost forgot!" He reached into his side pouch on his belt and produced a delicately carved purple bead. He held it out for her to look at." "I figured it would look just stunning in your hair darling and it's purple which would bring out your eyes. Well one of them at least." He snickered slightly and she rolled her eyes at the jest. His tail flicked with joy as they paused in their walking so that he could reach up and put the bead into a piece of her thick hair. He braided it in just like she had taught him so that it would stay and not fall out. 

"There!Absolutely lovely." 

As he pulled away his shirt rode up just enough and her hair was just long enough that before either of them knew was was happening Molly was bent over with a hand to his left nipple and Yasha was rubbing the side of her head where her hair had gotten pulled. 

"Ow ow ow oww!" he cursed in infernal and hissed through his teeth. It wasn't the worst pain he had ever felt, but it was like stubbing your toe in the early morning or whacking your shin on a wooden cart edge. It just made you want to curl into a ball. 

"Did you just get your piercing stuck on my hair?" Yasha was staring at him like this was something unexpected. It should have been perfectly expected in the circus. Especially with him.

"Ugh yes. They're still new too and your hair pulled on it. Fuck!" he rubbed tenderly around the sore area and pouted. It wasn't until he looked over that he noticed Yasha bent over at the waist laughing at his expense. His expression soured as he continued to rub the sensitive nub. "I told you not to get them done." She managed to choke the words out in between quite laughs.

"Look. They won't be that sore in a few weeks and that was an awkward way to catch them I'm sure it will be fine in the future. Who knows maybe they'll be a little fun." He waggled his eyebrows at her and she just huffed in amuesment. 

Neither of them mentioned the fact that he didn't even remember how sex worked and he hadn't even kissed anyone as far as his memories went. They both knew he had created an elaborate story about all the sexual encounters he'd had in his life. They both knew it was all lies. 

Molly liked that Yasha let him pretend. Pretending kept him from feeling empty.

_____________________________________________________________________

2\. The god damn bed sheets

 

If there is one thing that's worse than waking up from his nightmares. Its waking up from his nightmares with his nipple rings accidentally caught in the fabric of his bedroll.

The nightmares usually started the same, they were his earliest memory of about a year and a half ago and his worst by far. There is nothing quite like waking up to suffocating darkness and having your first breath tainted with gritty earth. It was terrifying and the more he pushed and prodded at the earth the more it came down on top of him and fell into his eyes and his mouth. 

This suffocating feeling was temporary though, the worst part was knowing what came after he surfaced. The blank vast and endless emptiness he felt inside. There was nothing left inside of him and it was the realization that there never had been anything that tore at every piece of him. 

Nothing. 

Blank.

Empty...

Empty, empty, empty... 

It was about at that point that the screaming started. There was nothing there, so his voice came out raw and pained in his throat as he yelled and screamed and clawed at the ground around him, some of his nails were cracked and chipped from the desperate climb out of the grave he had woken up in. 

The echoing sentiment of knowing that he had absolutely nothing to him was usually what startled him awake. 

With a desperate gasp Mollymauk hurtled back to consciousness and he yanked upwards from his bedroll. The sharp tug and pain he felt on his chest was what brought his brain back from the cliffs of the endless void that still occupied him. He winced and looked down blearily at the blankets that were caught by a single fucking thread on his right nipple piercing. 

"Fuck me." He gingerly set about unhooking the piece from his jewlery and rubbed at it softly. That moment was when Yasha made her usual appearance by poking her head into the tent. One look at his stricken face was enough and she was kneeling next to his bedroll and had one firm hand on his shoulder. 

"Hey." She didn't have to explain that she heard his screaming from her tent, or that he looked like death. They had already been through this routine and she was ready with her other hand to grasp his firmly as he leaned forward with a shuddering breath, the first of many that came in rapid succession. 

Most of them started to get hitched his his throat as hot wet tears melted down his face and his grip became almost harsh on her hand and shirt, but she said nothing and just held him close. Her hand moved up to stroke his almost chin length hair and he felt comforted by the motions. It got longer every week, his hair that was.

"Its okay. Mollymauk you're here its okay. Another nightmare?" He swallowed all of his fears, the emptiness and everything that haunted him and forced it into the hole in his chest. There was no time for feeling like this and no need to worry Yasha. He came up with three brand new stories; Where his first kiss had been, the first carnival he ever saw and the parents he grew up with making him dinner. The made up stories gave him strength and he focused on the bright colors the fantasies put into his head and swallowed the thickness in his throat. 

"No. I got my ring caught on the blankets." He sniffled slightly but pulled a smile to look up at Yasha. He lied, because it made him feel better. Her expression did not change except for the slightest of twitches of her lips upwards. 

"I see. Must have caught it pretty hard since you told me they were fully healed last week." He nodded solemnly and brought a hand up to rub at it dramatically. 

"It was really stuck. Will you kiss it to make it feel better?" He batted his eyelashes at her and she gave him a dead look before shaking her head. "No, it will heal fine on its own."

"But Yaaasha. I NEED it!" She rolled her eyes and stood up to leave the tent. 

"Goodnight Mollymauk Tealeaf." She left the tent as quietly as she had come in but he knew she used his full name deliberately and the warmness in his chest outweighed the dread in his heart and the pain in his right nipple. He snuggled back under the blankets and stared at the canvas wall until morning came, thinking a hundred fantastical things to distract himself from the empty.


	2. Chapter 2

**Notes for the Chapter:**

> Hello all! Please enjoy some more nipple ring shenanigans! ;D

3\. Setting up the Circus  
It is not long after that they find themselves in Trostenwald and their Carnival of curiosities runs into an even more curious group of people that band together. As Molly had said in the Tavern when he first met the group ‘If there was any group in need of a good time it was this sorry lot’. Especially the more than slightly dirty man that wore the long brown coat and sat with the truly intriguing green skinned individual. He looked like he'd had a night, and not the good kind. 

Molly had immediately been pulled in by his vibrant blue eyes, despite any of the dirt or grime that most people would have been repulsed by. After the initial shock from his eyes though, he could see faint bruising and some small scrapes and cuts along his jawline just under the scruffy beard and his knuckles peeked out with raw edges underneath the finger-less gloves he wore.

Molly spent more time than he would have liked staring at that man initially, but he came to the same conclusion as the rest of the lot in that tavern. They all needed to relax and have a good time. So, they invited them to the carnival, and Jester, Moonweaver bless her adorable soul, was the most excited in the entire group. 

Yasha and Molly returned to the carnival and continued to help Gustav and the crew set up for the opening event that evening. 

Molly was tough, he was not strong; but regardless he often tried to help Yasha with the actual setting up of large things when he had already gallivanted about the town and passed out as many fliers as he possibly could. They were working in tandem to lift some of the heavier beams that supported the big top but Molly was really just pretending to help. He was more than half sure that if he let the beam go it would actually be just fine sitting alone on Yasha's shoulder, but they enjoyed each other’s company and he wanted to gossip. 

"Yasha dear, what did you think of that wonderful group of misfits we ran into earlier? Think they'll come by for opening night?" Yasha was thoughtfully silent ahead of him for a time and Mollymauk swished his tail from side to side as he stared at her back, both arms up to ‘help’ carry the support beam.

"They were interesting." That was more than enough for Molly to springboard off of.

"Interesting indeed! That Jester is just adorable." Yasha nodded silently in agreement. "But did you see the interesting bloke in the tattered coat? He was about six different shades of brown on the outside but he was hiding the most brilliant oasis of blue I've ever seen. And he's travelling with a Goblin!"

"Molly what are you talking about?"

"The redhead." Yasha snorted with laughter and rolled her eyes where Molly couldn't see because he sounded like a little kid who had just found something new and shiny. She had to quickly remind herself that he was technically basing everything off of two years of experiences, meeting new people was still fun for him. 

"I see. What did you think about the uh... monk looking one?" Mollymauk had to pause to think about that for a second and he stopped walking. The log slid off his shoulder as Yasha continued forward, not even noticing the lack in help. 

"You mean the grumpy one with the attitude?" He grinned wide and sharp. "I'm sure she has at least one redeeming quality that isn't her fists." He was mostly joking but she had been quite abrasive at first. First impressions aside he could admire someone with physical strength but he hadn't spent much thought on her. Noticing now that Yasha was carrying the log completely by herself he sashayed over to her and held a hand up again, pretending to help lift the thing. 

"I'm interested in the half Orc, did you notice he didn't have tusks?" They both looked to the left where Bo was hammering one of the many stakes into the ground to hold the canvas of the bigtop down in case of any wind. He had a nice set of tusks from his bottom lip. 

"Maybe he didn't get the trait." Yasha stopped them at the entrance of the circus tent as Orna and Toya stepped out. They both nodded to the two and Mollymauk beamed a full faced grin at Toya who returned a shy smile and a wave of her hand. Molly was partial to her because he wanted to keep her safe, she was like a little sister to him in some regards and she liked his stories. It helped that someone liked his stories. Helped him keep his head on more or less.

Once the coast was clear they ducked through the flap with the support beam into the big top. The stands were being set up inside and Yasha carried the beam over to the last side of the tent that needed propping up, with his help of course. 

"Ah Yasha! Mollymauk I need to go over some things with both of you!" Gustav had just entered the tent and his timing could not have been worse. Yasha had just been setting the beam down with Molly's help and she dropped it to the ground vertically and suddenly when Gustav called their names and Molly happened to be right next to it. a piece of the wood splintered and by the bad luck of the devil the small piece of wood poked through his shirt making a nice hole and slid through the ring attached to his nipple. It became wedged around his nipple ring.

There are many words for the sensation of a sliver of wood trapping you to a large pole you can't lift by yourself through your nipple ring. ‘Fuck me’ were the first ones that came to Mollymauk's mind as he'd tried to pull away from the pillar only to feel the sharp tug on his right nipple as the ring was caught in the crack between the splintered piece and the actual wood. 

"Ah...Um. Yasha?" The burly woman had already walked over towards Gustav and they were both discussing safety measures for the show that night earnestly. 

Molly told himself that he was not embarrassed by the situation but his nervously twitching tail and dark purple cheeks told a completely different story.

"Molly what are you doing? I have to go over safety details, get over here." Molly swallowed and opened his mouth but no words came out. He was half crouched because of the placement of where the wood was pinching the ring and he was practically hugging the pole. He watched with mortified eyes as Yasha connected the dots and one of her eyebrow slowly raised upwards.

Fuck this shit.

"I um... Help." was all that he managed to squeak out as he tugged at the piece of wood to no avail. He was not very strong and the wood was sturdy for the reason that it was supposed to support the tent. Gustav was lost in the situation as Yasha walked steadily over with heavy footfalls to her friend.

"I don't understand what happened?" Gustav asked with a confused expression.

"Mollymauk is pinned to the post by his nipple ring." Her statement held no emotion but she said it loud enough that everyone in the big top heard it and if he hadn't been embarrassed before he definitely, one hundred percent was now. His face felt hot, and that was saying something considering how warm tieflings always were. His tail curled around his leg trying to hide and make him seem smaller as he frowned.

Luckily for him Yasha was a good friend and she was already there right next to him ready to help. 

"I am not pinned I am... just...stuck. It’s just caught on the fucking wood!" He tried to save face but Gustav laughing in the distance and the twins giggling to each other was not helping. Yasha leaned down close to his chest and lifted his shirt to check the damage. She hummed in thought and leveled him with one of her most serious stares.

"It looks serious. We might have to cut it off." The blood drained from his face as he stared at her and her words sunk in. 

"No. NO! Nonononono!!! WE’RE NOT CUTTING OFF MY NIPPLE!" Yasha let him panic for a few seconds before she huffed a short laugh and lifted the pole with a grunt. Molly squawked as the ring was pulled upwards by where it was pinched before gravity yanked it out of the wood and he was able to take a few steps back a hand to his chest already rubbing at the piercing. He narrowed his red eyes at his friend. 

"You are very mean sometimes." She set the pole down and shrugged with her arms out wide. 

"I can put you back on the pole." He gasped at her playfully his tail shooting straight outwards at the thought and put a protective hand over his chest.

"And they call ME the devil child!" Gustav had stopped laughing and reorganized himself as he called out to them. 

"You both are now get over here so I can finish putting all of this together and we can have a fantastic show tonight!" He reached out to try and shove Yasha playfully as they walked over to Gustav and it was a big mistake. It only took one hand and a decent shove on her part to send him stumbling to his left and almost falling over. He cursed in Infernal as he regained his balance and brushed off his shirt and cloak. The hole would have to be mended later.

Gustav sighed a painful sigh and gave them both looks. "Come on now serious time." Molly nodded but his wide and playful grin remained on his face, matched by the small upturn of Yasha lips.

_______________________________________________________________

4\. Cloaks and awkward encounters  
Losing the circus was almost detrimental to Mollymauk and unknown to his companions he was clinging desperately to the ragtag group they had made. Yasha had agreed to stay with him, obviously she would go off and do her own things but her word meant everything because it meant she was still here watching over him. However she was off Yashaing and he was here trying desperately to remember all of the colorful stories he had been telling himself about who he was just a week prior, while also staring down a certain dirt covered wizard from where he sat in the tavern. 

Molly was no stranger to attraction, he knew that he saw beauty in that man where he was sure that Caleb saw nothing of importance. The gentle slope of his nose wide nose and the curve of his lips as he formed each arcane word that he was reading silently from the pages of one of his books. The things those lips could probably do. Molly was clearly infatuated, he just didn’t know to what extent yet and Caleb was clearly not open to anything at the moment.

Slowly he slid his gaze away from the troubled wizard and instead looked from one member of the group to the others. Each of the faces was familiar to him now but so very strange. They all barely knew each other, but there was safety in numbers and the important thing was that they all stick together and watch their backs. Molly did feel like there was something with this group of people that he wanted to trust and believe in. He didn't yet believe in it, but maybe soon he would. 

After all he didn't have anything else to believe in. 

Caleb paused in his reading of the arcane text and Molly looked down towards his table so as to not be caught staring so blatantly. He swirled his ale in his flagon and leaned his head down after taking a hearty swig. He missed Yasha. 

"Mollymauk are you okay?" He jerked upwards as the object of his affections appeared directly next to his table. 

In the moment he jerked upwards he felt a pinching pain in his left nipple as his ring got caught on a loose thread of his coat. Maybe if his shirt hadn't been so open and his bare chest hadn't been exposed to the embroidery threads on the inside this wouldn't have happened. But it sure was happening and right in front of Caleb too. 

Molly felt his eyes water as he looked up at Caleb and oh this must have looked very strange indeed.

"Yes?" he had meant it to sound confident but it came out strangled and as more of a question than anything else. Caleb was giving him a very concerned look. 

"You don't sound okay. I was worried because you seemed away from the group but are you in pain?" Molly wanted to melt underneath the table and not exist. He sat up fully and another twinge of pain had him exhaling sharply as his coat moved on his shoulders. It went straight to his groin. FUCK. He had to fix this now or he was going to be incredibly hard in his pants in a matter or moments. 

"Not in pain, exactly. Something Just...Its caught...Ugh you know what?" He sat up and handed his tankard over to Caleb before reaching down to his coat. He opened the extravagant thing and blatantly fixed where the nipple ring had caught the loose thread. He paid no mind to how red Caleb's face was and instead rubbed at his nipple gently to try and make it feel less abused. 

“Wow that’s much better.” He said after the pain went away.

Molly cleared his throat and looked back up at Caleb.

"Sorry about that, so-" he broke off mid-sentence because Caleb was in the process of throwing back his entire tankard of ale in one go. His face was a bright red and Molly blinked as he slammed the tankard down, wiped his mouth and stood up. 

"Ja, glad you are okay." and with that Caleb walked briskly away from the table leaving Molly to stare after him in confusion and slight awe. He didn't know that Caleb was capable of drinking like that and frankly was a little confused as to why he was drinking so heavily at this time in the morning anyway. Huh weird.

Nott approached the table and gave him a distrustful look. She had her never-ending flask in her hand open.

"Where did Caleb go and what did you do?" Molly pointed silently towards the stairs and watched her leave as well. He stared at the table for a moment before heading back to the bar and ordering a new drink for himself. Fuck it! If everyone else was getting plastered in the early morning so was he!

He really needed to stop getting his nipple rings caught on things.

**Notes for the Chapter:**

> Comments are very appreciated and I hope this made you laugh just a little bit. I love writing lighthearted things because honestly these boys have been through a lot already. 
> 
> <3


End file.
